Details
| Original language | English |
|---|---|
| Pages (from-to) | 3041-3048 |
| Number of pages | 8 |
| Journal | European Journal of Organic Chemistry |
| Volume | 2017 |
| Issue number | 21 |
| Publication status | Published - 29 Mar 2017 |
Abstract
Transition-metal-catalyzed C–H functionalization is an emerging powerful alternative to ortho-lithiation protocols. For ferrocene systems almost exclusively noble-metal catalysts have so far been used. Herein we present the first examples of cobalt-catalyzed ortho-methylations by C–H activation at ferrocenes bearing various ortho-directing groups (ODGs). The cobalt-catalyzed ortho-methylation results in the formation of racemic 1,2-disubstituted ferrocenes in 21–89 % yield. In some cases symmetric 2,5-dimethylated ferrocenes prevailed or even were the only isolated products.
Keywords
- Cobalt, C–H activation, Ferrocene, Methylation, Sandwich complexes, Transition-metal catalysis
ASJC Scopus subject areas
- Chemistry(all)
- Physical and Theoretical Chemistry
- Chemistry(all)
- Organic Chemistry
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In: European Journal of Organic Chemistry, Vol. 2017, No. 21, 29.03.2017, p. 3041-3048.
Research output: Contribution to journal › Article › Research › peer review
}
TY - JOUR
T1 - Cobalt-Catalyzed ortho-Methylation of Ferrocenes Bearing ortho-Directing Groups by Catalytic Directed C–H Bond Activation
AU - Schmiel, David
AU - Butenschön, Holger
PY - 2017/3/29
Y1 - 2017/3/29
N2 - Transition-metal-catalyzed C–H functionalization is an emerging powerful alternative to ortho-lithiation protocols. For ferrocene systems almost exclusively noble-metal catalysts have so far been used. Herein we present the first examples of cobalt-catalyzed ortho-methylations by C–H activation at ferrocenes bearing various ortho-directing groups (ODGs). The cobalt-catalyzed ortho-methylation results in the formation of racemic 1,2-disubstituted ferrocenes in 21–89 % yield. In some cases symmetric 2,5-dimethylated ferrocenes prevailed or even were the only isolated products.
AB - Transition-metal-catalyzed C–H functionalization is an emerging powerful alternative to ortho-lithiation protocols. For ferrocene systems almost exclusively noble-metal catalysts have so far been used. Herein we present the first examples of cobalt-catalyzed ortho-methylations by C–H activation at ferrocenes bearing various ortho-directing groups (ODGs). The cobalt-catalyzed ortho-methylation results in the formation of racemic 1,2-disubstituted ferrocenes in 21–89 % yield. In some cases symmetric 2,5-dimethylated ferrocenes prevailed or even were the only isolated products.
KW - Cobalt
KW - C–H activation
KW - Ferrocene
KW - Methylation
KW - Sandwich complexes
KW - Transition-metal catalysis
UR - http://www.scopus.com/inward/record.url?scp=85020829502&partnerID=8YFLogxK
U2 - 10.1002/ejoc.201700358
DO - 10.1002/ejoc.201700358
M3 - Article
AN - SCOPUS:85020829502
VL - 2017
SP - 3041
EP - 3048
JO - European Journal of Organic Chemistry
JF - European Journal of Organic Chemistry
SN - 1434-193X
IS - 21
ER -